Arlan Hamilton’s blueprint for inclusive innovation

“Thanks for meeting me here,” said Backstage Capital’s Arlan Hamilton, as she greeted me with a fist bump in the lobby of the Four Seasons Hotel in Toronto. I’m a big fan of handshakes as a greeting. Hamilton is a germaphobe and doesn’t like shaking hands; she even got Al Gore to fist bump instead of shake her hand.

Just made @algore fist bump me instead of a handshake bc being an awesome human who is basically saving the world doesn’t stop you from having germs. (To his credit, he rolled with it) pic.twitter.com/8VJhqFLSqC

Hamilton was set to give a fireside chat at yesterday’s #movethedial Summit, but she made time for interviews throughout the day and in between meetings. Now that Backstage Capital has invested in over 100 founders (though no Canadians — yet) and Hamilton has graced the cover of Fast Company, she has no shortage of demands on her time.

Tucked in a corner of the lobby with loud jazz fusion music playing, Hamilton shared her insights on founder self-education, the difference between being a fan versus being an ally, and hints about the future of Backstage.

Why founders should befriend Google before asking for money

“Let your lack of knowledge be the last issue you have,” Hamilton said as we talked about her strong stance that founders need to do their own digging before going into VC meetings and asking for money.

In a lengthy Twitter thread, Hamilton lamented how founders will approach her asking for mentorship, advice, or investment, but she’ll be able to tell them more about their own business or industry than they can. The kicker? Hamilton is often a relative novice in the business in question.

2/I’m noticing so many aspiring entrepreneurs I’m meeting are asking me for advice or to be their mentor, but when I ask them about certain basic references that in their lane, they’re not familiar. You have to be on a RELENTLESS pursuit of data and knowledge.

“I’m looking at them and saying, ‘Do you understand what the competition looks like? How the best founders I know are training for their moment?’”

To these people, she has one simple word: no. “I have to demand more of you. It’s only going to get tougher. Even with money, it becomes bigger problems, tougher problems, and more money problems.”

When it comes to knowledge, though, Hamilton is quick to say this isn’t about impressing anyone, nor is it about the idea that underrepresented folks (“underestimated,” as she and Blendoor founder Stephanie Lampkin say) need to be “ten times as good to be considered equal.”

It’s not even about having the same style of education across the board, since some people learn better by reading versus overhearing, and vice versa. Self-education, for Hamilton, is about power and control.

“Of all the things we can’t control in life, we can control the amount of information we take in,” she said. “[I] can control that tomorrow I am going to research this thing and know more than I knew yesterday. That’s really powerful, so why not take advantage of it?”

Fans and allies

“We’re gonna need each other. You need me. I need you. There’s no reason to be drawing a line in the sand.”

“It’s so much easier to advocate for others than yourself.”

When we get to talking about intersectionality – the topic that really gets Hamilton excited when we discussed making entrepreneurship more inclusive – she was quick to bring up a story about how she learned to cut others some slack through an embarrassing personal gaffe.

“There was an Asian man that came up to me at an event, and I called him by the name of another Asian man in venture [capital],” she said. “I did to him what people do to me and [when it happens to me] I get upset and automatically assume they are horrible people for assuming I’m another Black woman. And I called myself out – so it’s giving a little bit of space and leeway [to allies who make mistakes]. If they are in the room, cut them some slack. They are taking a step that a lot of people aren’t taking.”

And as much as someone needs to be an ally, there’s more to it, and individuals have to be aware of who looks like they might be an ally versus who really is one.

During Lampkin’s talk at the Summit breakfast, she shared a video of herself on a popular US pitch show. The judges – two white men, one white woman, and one Asian woman – watched her pitch. Only the men wanted to learn more, while the women said they didn’t believe she had a viable business. Lampkin used that example to highlight that not everyone who looks like they would support you actually does, a point that Hamilton later brought up again during our interview.

“I think in the next six months, my challenge will be about being the best leader I can be.”

She demonstrated the example by referencing a popular trans woman who spoke about the difference between being a fan versus being an ally.

Being a fan, said Hamilton referencing the video, is telling a trans woman she looks great or her dress is amazing (The official phrase used in the video was “Yas girl.”)

Being an ally, on the other hand, was about presence during the rough times – when she (the trans woman) couldn’t speak up for herself. When she was talking about needing health insurance. When she was in an unsafe space and needed help.

Of course, you can also be both your own fan and your own ally. But doing it for yourself is where things get tougher.

“It’s so much easier to advocate for others than yourself,” said Hamilton.

However, she takes that personal truth and spins it. Lampkin and others often said throughout the Summit that standing up for yourself is actually “chiseling away” so the next person will have an easier time. Self-advocacy may not work for the advocate personally, but it will help the next person, explained Hamilton. And that, for her, is a strong enough business case.

Backstage in the New Establishment

While Hamilton undoubtedly gained international fame as one of only a handful of Black women to be on the cover of a mainstream magazine (and one of an even smaller handful when you remove fashion magazines), it can be easy to overlook that Hamilton was also ranked in the 2018 New Establishment List by Vanity Fair, signalling her shift into the spotlight as more than just a flash in the pan.

For the past six years, Hamilton was not a well-known name and Backstage Capital was not a well-known business. She spent that time learning and fundraising. She faced all the traditional hurdles a startup founder will have, such as having to explain herself at every turn, on top looking for deal flow and helping companies grow to prove out your thesis.

But with the mounting press requests now – her agent has been busy – and the ever-growing profile of the formerly-homeless Black woman venture capitalist, she’s optimistic about the corner she’s about to turn.

“I think in the next six months, my challenge will be about being the best leader I can be,” she said. “There’s something very, very special about the culture at Backstage with thirty-plus people and over one hundred [portfolio] companies. It’ll be ‘how do we maintain that magic we have that we so love?’.”

The team went from seven people to over 30 in the past year. Hamilton projects that could double again in the coming year. For the past six years, Hamilton has been fundraising, always adding runway at the last second in order to continue her mission. Now she’s close to a full runway and already has a growing team. With everyone now paying attention, she’s going to do everything she can to make a dent in the universe.

Stefan is a Toronto-based entrepreneur and writer passionate about the people behind tech. He's interviewed over 100 entrepreneurs on topics like management, scaling, diversity and inclusion, and sharing their personal stories. Follow him on Twitter @stefanpalios or send an email to stefan.palios@gmail.com.